Winship combines private legal practice experience with over thirty years of director level management experience in the student transportation industry, primarily with the Anne Arundel County Public Schools.  His current professional focus is related to consulting activities within the student transportation arena, and he further serves as Of Counsel for the law office of Hillman Brown and Darrow, P.A., Annapolis, Maryland.

Winship recently completed an eight (8) year term on the Board of Directors at Providence Center, Inc, a non-profit entity primarily engaged in providing key services to adult aged developmentally limited persons residing in Anne Arundel County, Maryland.  

Winship has been a member of the Board of Directors, serving presently as Treasurer, of the Annapolis Film Festival, Inc., since October 2020.